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Enzymes for Prodrug-Activation in Cancer Therapy
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2020
Another melanoma treatment strategy focuses on prodrugs that are activated by the tyrosinase enzyme which is upregulated within malignant melanomas/mutant melanocytes compared with healthy melanocytes, hence providing an in-situ tool for the activation of melanoma prodrugs (Jawaid et al., 2009). Perry et al. (2009) developed and characterized a range of triazene derivatives as prodrug candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). The prodrugs contained a tyramine or dopamine promoiety required for tyrosinase activation, joined via an urea functional group to the cytotoxic triazene. Recently Sousa et al. (2017) reported the synthesis of new DNA-alkylating triazene derivatives containing hydroxyphenylalkyl carboxylic acids, activated by tyrosinase for application to a melanoma-specific therapy. The investigations included structure-activity relationship studies enabling the identification of optimal structural features for enzyme affinity.
Health and Safety Information
Published in W. M. Haynes, David R. Lide, Thomas J. Bruno, CRC Handbook of Chemistry and Physics, 2016
W. M. Haynes, David R. Lide, Thomas J. Bruno
Decabromobiphenyl 2,4-Diaminoanisole sulfate 4,4'-Diaminodiphenyl ether 4,4'-Diaminodiphenylmethane 4,4'-Diaminodiphenylmethane dihydrochloride 4,4'-Diaminodiphenyl sul de cis-Diamminedichloroplatinum Dibenz[a,h]acridine Dibenz[a,j]acridine Dibenz[a,h]anthracene 7H-Dibenzo[c,g]carbazole Dibenzo[a,e]pyrene Dibenzo[a,h]pyrene Dibenzo[a,i]pyrene Dibenzo[a,l]pyrene 1,2-Dibromo-3-chloropropane 1,2-Dibromoethane 2,3-Dibromo-1-propanol 2,3-Dibromo-1-propanol, phosphate (3:1) p-Dichlorobenzene 3,3'-Dichloro-p-benzidine 3,3'-Dichloro-p-benzidine dihydrochloride 1,2-Dichloroethane Dichloromethane 1,3-Dichloropropene (unspeci ed isomer) Diethyl sulfate 2,3-Dihydro-6-propyl-2-thioxo-4(1H)pyrimidinone 1,8-Dihydroxy-9,10-anthracenedione 3,3'-Dimethoxybenzidine 4-(Dimethylamino)azobenzene 2',3-Dimethyl-4-aminoazobenzene Dimethylcarbamic chloride 1,1-Dimethylhydrazine Dimethyl sulfate 1,6-Dinitropyrene 1,8-Dinitropyrene 1,4-Dioxane 1,2-Diphenylhydrazine 1,3-Diphenyl-1-triazene Disperse Blue No. 1 Doxorubicin hydrochloride Epichlorohydrin 1,2-Epoxy-4-(epoxyethyl)cyclohexane Ethyl carbamate Ethyl methanesulfonate N-Ethyl-N-nitrosourea Fluoroethene Fuchsin Furan Glass wool bers (inhalable) Hexabromobiphenyl (unspeci ed isomer) Hexachlorobenzene 1,2,3,4,5,6-Hexachlorocyclohexane, (1,2,3,4,5,6) 1,2,3,4,5,6-Hexachlorocyclohexane, (1,2,3,4,5,6)
N,N,N-Heterocycles
Published in Navjeet Kaur, Metals and Non-Metals, 2020
Carbon-hydrogen activation of aryl triazene compounds followed by intramolecular amination at moderate temperature in catalytic amounts of palladium acetate is one of the methods of synthesizing 1-aryl-1H-benzotriazoles (Scheme 77) [138].
Synthesis, structure, magnetic and electrocatalytic properties of a dinuclear triazendio-copper(II) complex
Published in Inorganic and Nano-Metal Chemistry, 2021
Hao Yang, Juan Du, Chun-Li Wang, Ze-Hao Xie, Shu-Zhong Zhan
Obviously, [Cu2(L)4] shows more active than the reported complexes, including a dinuclear cobalt(II) complex of 1-[(2-methoxy)phenyl]-3-[benzothiazole] triazene ligands. The TOF for hydrogen evolution from acetic acid was 32.1 mol H2/mol catalyst/h, and the OP was 942 mV,[36] and a dinuclear triazenido–copper(II) complex with 1,3-bis[(4-chloro)phenyl]triazene ion coordination. The TOF for hydrogen evolution from acetic acid was 43 mol H2/mol catalyst/h, and the OP was 942 mV.[34] However, it is lower than the dinuclear copper(I) complex of 1, 1-[(2-methoxy)phenyl]-3-[2-(chloro)phenyl] triazene ligands. The TOF for hydrogen evolution from acetic acid was 65 mol H2/mol catalysts/h, and the OP was 942 mV.[35] These results show that metal centers play a role in determining the catalytic activities of the molecular catalysts.
Synthesis and properties of 1,3-bis[(2-bromo)benzene]triazene and its binuclear silver complex
Published in Inorganic and Nano-Metal Chemistry, 2020
Qian-Ya Xie, Wei-Xia Liu, Shu-Zhong Zhan, Xiao-Lan Wei
People still focus a great deal of attention on transition metal complexes with varying ligands due to their potential uses as catalysts, biological processes and inorganic materials.[1–3] Metal ions can be framed in special position by using appropriate organic ligands, controlling the electron withdrawal from the metal ion core.[4] Anionic, bridging, nitrogen bonded ligands, such as triazenides have attracted our attention, since they show a variety of bonding modes with distinct properties.[5–11] Additionally, triazenide ligands also can stabilize late transition metal complexes containing metal-metal bonds.[12,13] Based on that the formation of triazenido-metal complex can affect luminescent behavior of the triazenido compound,[14–16] triazenido species can serve as potential fluorescent sensors for metal ions. Within this mind, a new triazenido compound, 1,3-bis[(2-bromo)benzene]triazene (HL) has been designed and synthesized in our Lab. In the presence of Et3N, the reaction of HL and AgNO3 afforded a binuclear triazenido complex, [Ag2(L)2]. In this article, we report the synthesis, characterization and properties of the triazenido compound, 1,3-bis[(2-bromo)benzene]triazene (HL), as well as the electrocatalytic behavior for hydrogen evolution of the silver complex, [Ag2(L)2] thereof.
Synthesis, characterization, luminescent, and catalytic performance of a dinuclear triazenido–silver complex
Published in Journal of Coordination Chemistry, 2018
Su-Ping Luo, Jia-Mei Lei, Shu-Zhong Zhan
The reaction of ethyl anthranilate, sodium nitrite, and 2-aminobenzothiazole gave a triazenide compound (HL) in 49% yield (Scheme 1). As shown in Figure S1, the 1H NMR spectrum of HL showed singlet of triazene group hydrogen atom at 13.06 ppm, in agreement with the structural analysis for triazene. 1H resonances were found in the range of 8.1–7.1 ppm for the aromatic protons, and at 4.43 and 1.44 ppm for the ethyl group. In the presence of Et3 N, the reaction of HL and AgNO3 provided a new silver complex, [Ag2(L)2], in 68% yield (Scheme 1). Silver(I), which has the d10 configuration, is expected to exhibit diamagnetic behavior. From Figure S2, the 1H NMR spectrum of the silver complex was indicative of a single-ligand environment. These results are also in agreement with the following X-ray photoelectron spectroscopy (XPS) analysis. As shown in Figure 1, the XPS spectrum of 1 showed two peaks at 366.8 and 372.8 eV, which are assigned to Ag+ 3d5/2 and 3d3/2, respectively, a typical characteristic of Ag(I) oxidation state. This is consistent with the results reported in the literature [25, 26].